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PubMed1984

Potential mutagenic activity of some vitamin preparations in the human gut.

Rutin is a nonmutagenic flavonol glycoside, whereas its aglycone quercetin is mutagenic. Cell-free preparations from fecal cultures (fecal preparations) contain a beta-glucosidase that, when incubated with rutin, hydrolyzes it to quercetin. This activity can be further induced when rutin is added to the fecal culture from which the cell-free preparation is made. When vitamin pills that contain rutin are added to the cultures, this induction is equally effective. The vitamin extracts by themselves, like rutin, were nonmutagenic; however, when the vitamin extracts were incubated with fecal preparations containing induced beta-glucosidase, a great increase in mutagenicity was observed.

Humans↗

PubMed1981

Antitumor activity of flavonoids on NK/Ly ascites tumor cells.

Among the various flavonoids, rutin and quercetin increased the survival time of mice inoculated with NK/Ly ascites tumor cells. The best results were obtained when the mice were given 2.0 mg rutin twice daily for 8 days. The O-silyl-substituted rutin and quercetin were less effective than rutin or quercetin themselves. Besides rutin, quercetin and morin two other flavonoids, luteolin and pelargonidin also exerted growth inhibitory effects on NK/Ly ascites tumor cells cultures in vitro.

Animals↗

PubMed1995

Virucidal short wavelength ultraviolet light treatment of plasma and factor VIII concentrate: protection of proteins by antioxidants.

The use of solvent/detergent mixtures and various forms of heat treatment to inactivate viruses has become widespread in the preparation of blood derivatives. Because viruses that lack lipid envelopes and/or are heat resistant, eg, hepatitis A virus (HAV) or parvovirus B19 may be present, the use of two methods of virus elimination that operate by different mechanisms has been advocated. We now report on short wavelength ultraviolet light (UVC) irradiation for virus inactivation and enhancement of its compatibility with proteins by quenchers of reactive oxygen species (ROS). Treatment of an antihemophilic factor (AHF) concentrate or whole plasma with 0.1 J/cm2 inactivated 10(5) to > or = 10(6) infectious doses (ID) of encephalomyocarditis virus (EMCV), HAV, bacteriophage M13, vesicular stomatitis virus (VSV), and porcine parvovirus. However, the recovery of factor VIII was 30% or lower on treatment of an AHF concentrate and 60% on treatment of plasma. Factor VIII recovery could be increased with little or no effect on virus kill by addition of rutin, a flavonoid known to quench both type I and type II ROS. On treatment of plasma in the presence of rutin, the recovery of several other coagulation factors was also enhanced by rutin addition and typically exceeded 75%. Electrophoretic analysis of treated AHF concentrate confirmed the advantage of rutin presence; UVC irradiation of plasma did not cause discernible changes in electrophoretic banding patterns, even in the absence of rutin. We conclude that addition of UVC treatment to existing processes used in the manufacture of blood derivatives will provide an added margin of safety, especially for nonenveloped or heat-stable viruses.

Animals↗

PubMed2001

Effects of flavonols on the generation of superoxide anion radicals by xanthine oxidase and stimulated neutrophils.

The effects of three aglycon flavonols (myricetin, quercetin, and kaempferol) and the natural glycoside rutin on superoxide anion radical generating systems were investigated. Quercetin, myricetin, and kaempferol inhibited the formation of uric acid from xanthine by xanthine oxidase, while rutin was ineffective. The generation of superoxide anion radicals by this system was determined by either reduction of cytochrome c or Pholasin luminescence. A scavenging of superoxide was only observed for myricetin and to a small extent for rutin. All flavonols tested inhibited the Pholasin luminescence of fMet-Leu-Phe-stimulated neutrophils. Rutin influenced the oxidative burst of neutrophils in the same way as wortmannin and LY294002, two inhibitors of the phosphoinositide 3-kinase gamma. Indeed, rutin inhibited the activity of this enzyme, whereas the three other flavonols showed no effect. Thus, an inhibition of enzymes involved in signaling rather than a scavenging of superoxide anion radicals dominates in fMet-Leu-Phe-stimulated neutrophils exposed to flavonols.

Cytochrome c Group↗

PubMed2003

Influence of a sugar moiety (rhamnosylglucoside) at 3-O position on the reactivity of quercetin with whey proteins.

The reaction of whey proteins (WP) with quercetin and rutin (quercetin-3-O-rhamnosylglucoside) is influenced by the glycosidic bound sugar moiety. The protein derivatives formed showed a blocking of tryptophan (max. 49%), free amino (max. 32%) and thiol groups (max. 24%). The amount of quercetin and rutin bound covalently (up to 94 and 31nmol mg(-1), respectively) was estimated by their characteristic absorbance between 300 and 340 nm. At least one molecule of the phenolic reactant was covalently bound to a beta-lactoglobulin molecule (beta-Lg). High molecular protein fractions were detected by SDS-PAGE (cross-linking with quercetin). All results confirm that quercetin is more reactive than rutin. The pH-dependent solubility of the derivatives decreased, although their hydrophilic character increased. The structural changes (circular dichroism (CD)) showed that especially rutin causes perturbation of the secondary (decrease of alpha-helix elements accompanied by an increase in random coil) and tertiary structure. The in vitro proteolytic digestibility, especially of the rutin derivatives was elevated, due to an increase in denaturation of the derivatives.

Chromatography, High Pressure Liquid↗

PubMed1983

Role of antigen structure in the regulation of IgE isotype expression.

Tobacco glycoprotein (TGP) is a glycoprotein containing rutin-like polyphenol groups that is purified from cured tobacco leaves and can be detected in condensates of tobacco smoke. One-third of normal humans have been shown to manifest immediate, IgE-mediated, wheal and flare reactions to an intradermal injection of TGP. Rutin-like moieties are also found in a wide variety of vegetable foods. The possible importance of sensitivity to TGP in the pathogenesis of the vascular and pulmonary complications of tobacco smoking has stimulated us to study the immune response of mice to TGP and the role of rutin groups in influencing isotype expression. A series of three intradermal injections of TGP elicits a long-lasting IgE antibody response in mice. However, no hemagglutinating antibodies are produced. Similarly, immunization with a rutin derivative of bovine serum albumin stimulates IgE antibodies to bovine serum albumin but little hemagglutinating antibodies. In contrast, mice injected in the same manner with bovine serum albumin produce both IgE and hemagglutinating antibodies. Thus, the rutin moiety is implicated as exerting a regulatory effect on isotype expression by suppressing the production of serum antibodies of isotypes other than IgE. The immunization procedure employed (which involves an initial injection of 100 micrograms of antigen in phosphate-buffered saline, followed, at monthly intervals, by two intradermal injections of 100 micrograms of antigen precipitated on alum) apparently fails to stimulate the normal "down-regulation" of the IgE response so that a persisting high-titered response is obtained.

Animals↗

PubMedDate not supplied

Scavenger effect of flavonols on HOCl-induced luminol chemiluminescence.

Hypochlorous acid (HOCl), the main product of the myeloperoxidase system, is a strong oxidant and a potent chlorinating agent, which can damage host tissues. In the present work, the scavenger effect of three aglycone flavonols (myricetin, quercetin and kaempferol) and of the natural glycoside flavonol, rutin, was studied towards HOCl using luminol-dependent chemiluminescence (CL). At 1 micro mol/L fi nal concentration, rutin was the most powerful scavenger of HOCl with an inhibitory luminol oxidation of 91.4% +/- 3.2%. Quercetin, kaempferol and myricetin inhibited the luminol-dependent CL at the same concentration only by 75.9% +/- 3.4%, 57.7% +/- 5.3% and 43.3% +/- 3.5%, respectively. With increasing concentration of these flavonols, a dose-dependent inhibition of luminol CL was observed. In order to prove to what extent flavonols scavenge HOCl, their concentrations that gave 50% inhibition of luminescence (IC50) were compared to IC50 values of the sulphur-containing compounds N-acetyl cysteine (NAC) and taurine. The scavenging activities of compounds tested decrease in the order: rutin > NAC > quercetin > kaempferol > taurine. The present study revealed that rutin was the most effective scavenger agent.

Acetylcysteine↗

PubMed1993

Is superoxide an initiator of microsomal lipid peroxidation?

The effects of "pro-oxidant" quinones, doxorubicin, Fe(3+)-ADP-doxorubicin complex, and menadione, as well as of free radical scavengers possessing superoxide-dismuting activities, Fe(3+)-rutin and Cu(2+)-rutin, on superoxide production and lipid peroxidation in rat liver microsomes have been studied. All quinone compounds efficiently suppressed lucigenin-dependent chemiluminescence produced in NADPH-dependent microsomal lipid peroxidation, but exhibited different effects on cytochrome c reduction: doxorubicin and Fe(3+)-ADP-doxorubicin weakly inhibited and menadione enhanced it. In accord with previous findings, menadione inhibited malondialdehyde (MDA) formation in microsomes, while Fe3-ADP-doxorubicin enhanced it. Efficiency of inhibition of MDA formation by the Fe(3+)-rutin and Cu(2+)-rutin complexes correlated well with their superoxide-dismuting activities in contrast to the findings obtained in nonenzymatic liposomal peroxidation, where the formation of superoxide ion is not expected. On these grounds, we propose that superoxide ion is an obligatory initiation species in microsomal lipid peroxidation; the effects of pro-oxidant quinones on lipid peroxidation depends on their ability to chelate iron ions and not on their redox-cycling activities.

Acridines↗

PubMed1983

Inhibition of Ca2+-transport ATPase from synaptosomal vesicles by flavonoids.

The inhibitory action of the flavonoid quercetin has been examined on the calcium-transport ATPase of synaptosomal vesicles and compared to that of two other flavonoids, morin and rutin. We have found that while quercetin caused a 50% inhibition of calcium transport at a concentration of 15 microM, morin and rutin had similar effects at concentrations of about 200 microM. A similar order of potency was observed also for ATP hydrolysis, though at higher concentrations. Quercetin also strongly inhibited phosphorylation of membrane proteins by ATP in synaptosomal vesicles. Rutin and morin had an almost negligible effect on membrane protein phosphorylation. The order of inhibitory potency of the flavonoids on the Ca2+-transport ATPase from synaptosomal vesicles: quercetin greater than morin greater than rutin, could be linked to their possible solubility in the membrane lipid phase since: (1) it paralleled their partitioning between a mixture of oil and water; (2) it paralleled their uptake from the reaction mixture by synaptosomal vesicles and phosphatidylcholine liposomes; (3) they had almost equal potency as inhibitors of the water soluble system of histone phosphorylation by protein kinase.

Animals↗

PubMed1995

Flavonoids as antioxidant agents: importance of their interaction with biomembranes.

Flavonoids, a group of phenolic compounds widely occurring in the plant kingdom, have been reported to possess strong antioxidant activity. In the present study, four flavonoids (quercetin, hesperetin, naringenin, rutin), chosen according to their structural characteristics, were tested in two different in vitro experimental models: (1) Fe(2+)-induced linoleate peroxidation (Fe(2+)-ILP), by detection of conjugated dienes; and (2) autooxidation of rat cerebral membranes (ARCM), by using thiobarbituric acid for assay of free malondialdehyde production. The results obtained were also interpreted in the light of flavonoid interactions, studied by differential scanning calorimetry, with dipalmitoylphosphatidylcholine (DPPC) vesicles as a biological membrane model. The antilipoperoxidant activity of the flavonoids tested can be classified as follows: rutin > hesperetin > quercetin > naringenin in the Fe(2+)-ILP test: quercetin > rutin > hesperetin > naringenin in the ARCM test. Quercetin, hesperetin, and naringenin interacted with DPPC liposomes causing different shifts, toward lower values, of the main transition peak temperature (Tm) typical for DPPC liposomes; however, no change in Tm of DPPC dispersion was observed in the presence of rutin. The hypothesis will be discussed that flavonoid capacity to modify membrane-dependent processes, such as free-radical-induced membrane lipoperoxidation, is related not only to their structural characteristics but also to their ability to interact with and penetrate the lipid bilayers.

Animals↗

PubMed2006

The effect of flavonoids on rat heart mitochondrial function.

In this study the effects of flavonoids (quercetin and its derivatives as rutin, hyperoside, quercitrin) on the oxidative phosphorylation in rat heart mitochondria were investigated. We found that all investigated flavonoids possessed uncoupling activity. Thus, quercetin, rutin, and quercitrin in dose-dependent manner induced a stimulation of the State 2 respiration rate by 10-110% with pyruvate + malate as substrate. The maximal stimulation of the State 2 respiration rate was obtained at 1.08 ng/ml of quercetin, 15.2 ng/ml of hyperoside and 44.4 ng/ml of rutin. Quercitrin had clearly lower effects. The State 3 respiration rate was also affected by flavonoids. Quercetin (from 1.08 ng/ml), hyperoside (from 10 ng/ml) and rutin (from 60 ng/ml) caused the decrease in State 3 respiration rate by 16-51%. We assume, that partial mitochondrial uncoupling (without affecting the State 3 respiration rate) induced by flavonoids could have a cardioprotective effect, and that mitochondria could be involved in the mechanism of this process.

Animals↗

PubMed2004

Effect of acyl donor chain length and substitutions pattern on the enzymatic acylation of flavonoids.

Rutin and esculin were enzymatically acylated with different aliphatic acids as acyl donors (fatty acids, dicarboxylic acids and omega-substituted fatty acids) by an immobilized lipase from Candida antarctica. The effect of the water content and the acyl donors pattern on the flavonoid initial acylation rate and conversion yield were investigated. The obtained results indicated that the water content of the medium has a strong effect on the performance of these reactions. The best conversion yields were reached when the water content was kept lower than 200 ppm. At low water content of the medium, these syntheses are influenced by carbon chain length and substitution pattern of the acyl donors. Higher conversion yields of esculin and rutin (>70%) were obtained with aliphatic acids having high carbon chain length (>12). Moreover, it has been found that the amine and thiol groups on omega-substituted fatty acid chain were unfavourable to these reactions. The 1H NMR and 13C NMR analyses of some synthesized esters (esculin and rutin palmitate) show that only monoesters were produced and that the esterification takes place on the primary OH of glucose moiety of the esculin and on the secondary 4"'-OH of the rhamnose residue of rutin.

Acylation↗

PubMed2006

Use of ionic liquids as media for the biocatalytic preparation of flavonoid derivatives with antioxidant potency.

Biocatalytic preparation of acylated derivatives of flavonoid glycosides was performed using various immobilized lipases in two different ionic liquids, namely 1-butyl-3-methylimidazolium tetrafluoroborate ([bmim]BF(4)) and 1-butyl-3-methylimidazolium hexafluorophosphate ([bmim]PF(6)). The influence of various reaction parameters on the performance and the regioselectivity of the biocatalytic process was pointed out, using as model reaction the acylation of naringin and rutin with vinyl butyrate, catalyzed by immobilized Candida antarctica lipase at 60 degrees C. The biocatalytic modification of flavonoids strongly depended on the ionic liquid used, the molar ratio of substrates, as well as the acyl donor chain length. The highest conversion yield (about 65% after 96 h of incubation) was obtained with short chain acyl donors (up to four carbon atoms), at a relatively high molar ratio (10-15) in both ionic liquids used. The amount of monoacylated flavonoid derivatives produced in a single-step biocatalytic process in [bmim]BF(4) was up to 5.5 g/L for monoacylated rutin and 30 g/L for monoacylated naringin. The regioselectivity of the process was higher in [bmim]BF(4) than in [bmim]PF(6) or organic solvents. Reaction rates observed in ionic liquids were up to four times higher than those reported for organic media. The acylation of sugar moiety of rutin with various acyl donors affected its antioxidant potential towards both isolated LDL and total serum model in vitro. A significant increase of antioxidant activity was observed for rutin-4'''-O-oleate.

Acylation↗

PubMed2005

Pro-oxidative effect of beta-carotene and the interaction with flavonoids on UVA-induced DNA strand breaks in mouse fibroblast C3H10T1/2 cells.

It has been suggested that beta-carotene itself is unstable under certain conditions and that a combination of antioxidants may prevent the pro-oxidative effects of beta-carotene. Thus, the present study aimed to investigate the interaction of beta-carotene with three flavonoids-naringin, rutin and quercetin-on DNA damage induced by ultraviolet A (UVA) in C3H10T1/2 cells, a mouse embryo fibroblast. The cells were preincubated with beta-carotene and/or flavonoid for 1 h followed by UVA irradiation, and DNA damage was measured using comet assay. We showed that beta-carotene at 20 microM enhanced DNA damage (by 35%; P<.05) induced by UVA (7.6 kJ/m2), whereas naringin, rutin and quercetin significantly decreased UVA-induced DNA damage. When each flavonoid was combined with beta-carotene during preincubation, UVA-induced cellular DNA damage was significantly suppressed and the effects were in the order of naringin > or = rutin > quercetin. The flavonoids decreased UVA-induced oxidation of preincorporated beta-carotene in the same order. Using electron spin resonance spectroscopy, we showed that the ability of these flavonoids to quench singlet oxygen was consistent with protection against DNA damage and beta-carotene oxidation. All three flavonoids had some absorption at the UVA range (320-380 nm), but the effects were opposite to those on DNA damage and beta-carotene oxidation. Taken together, this cell culture study demonstrates an interaction between flavonoids and beta-carotene in UVA-induced DNA damage, and the results suggest that a combination of beta-carotene with naringin, rutin or quercetin may increase the safety of beta-carotene.

Animals↗

PubMed2005

The rutin/beta-cyclodextrin interactions in fully aqueous solution: spectroscopic studies and biological assays.

In the present work the feasibility of beta-cyclodextrin complexation was explored, as a tool for improving the aqueous solubility and antioxidant efficacy of rutin. By means of 1H NMR, UV-vis and circular dichroism spectroscopy the single aromatic ring of rutin was found to be inserted into the beta-cyclodextrin cavity to form a 1:1 inclusion complex. The effect of beta-cyclodextrin on the spectral features of rutin was quantitatively investigated, in fully aqueous medium, by holding the concentration of the guest constant and varying the host concentration. The associated binding constants were estimated to be 142+/-20 and 153+/-20 M(-1), respectively, on the basis of the observed UV-vis absorption and circular dichroism intensities. The antioxidant activity of rutin was also investigated, as affected by molecular encapsulation within beta-cyclodextrin (batophenanthroline test; comet assay; lipid peroxidation); the inclusion complex revealed improved antioxidant efficacy that may be in part explained by an increased solubility in the biological moiety.

Animals↗

PubMed1997

Protective effect of flavonoids on doxorubicin-induced cardiotoxicity.

We have examined the effect of alpha G-Rutin and luteolin on doxorubicin (DOX) toxicity in mice. In the heart, the lipid peroxide level, increased to 1.5 times of the normal level induced by DOX, decreased to the normal level after treatment with alpha G-Rutin or luteolin (i.p.). Glutathione peroxidase (GSHpx) activity, decreased to 73% of normal activity after DOX treatment, was shown to recover by the combined flavonoids. The lipid peroxide level in bone marrow cells increased to 5.9 times of the normal level by DOX treatment, whereas this level in the extra bone marrow cells did not change by treatment with DOX. The combination of alpha G-Rutin and luteolin with DOX significantly inhibited the DOX induced-increment of the lipid peroxide level in bone marrow cells. Flavonoids have also reduced the effect of DOX toxicity by oral administration. It is suggested that it is possible to reduce DOX toxicity by the intake of food including flavonoids. In NADPH-dependent lipid peroxidation, alpha G-Rutin and luteolin showed concentration-dependent inhibition. Therefore, we considered that the reduction effect of DOX toxicity by flavonoids was caused by antioxidative action and other effect of the flavonoids.

Administration, Oral↗

PubMed2003

Neuroprotective effect of antioxidants on ischaemia and reperfusion-induced cerebral injury.

The present study is designed to investigate the effect of dietary flavanoid rutin, micronutrient selenium and garlic oil on ischaemia and reperfusion-induced cerebral injury. Global cerebral ischaemia was induced by occluding right and left common carotid arteries for 10min followed by reperfusion for 24h. Cerebral infarct size was estimated using triphenyltetrazolium chloride staining. Elevated plus maze was employed to estimate short-term memory. Degree of motor incoordination was evaluated using inclined beam-walking test and lateral push test. Mitochondrial thiobarbituric acid reactive substances (TBARS) assay was employed as an index of oxidative stress. Global cerebral ischaemia followed by reperfusion produced a significant impairment in short-term memory and motor coordination and produced a notable increase in mitochondrial TBARS. Administration of rutin and garlic oil before global cerebral ischaemia markedly reduced cerebral infarct size and attenuated impairment in short-term memory and motor coordination. Administration of sodium selenite either before or after global cerebral ischaemia markedly reduced cerebral infarct size and attenuated impairment in short-term memory and motor coordination. The protective effect of rutin, sodium selenite and garlic oil was accompanied by a marked decrease in mitochondrial TBARS. On the basis of these results, it may be suggested that rutin and garlic oil administrated before cerebral ischaemia may scavenge reactive oxygen species and consequently attenuate global cerebral ischaemia and reperfusion-induced cerebral injury. Sodium selenite administrated before and after cerebral ischaemia may be neuroprotective due to its antioxidant effect.

Allyl Compounds↗

PubMed2004

Crystal structure of human prostaglandin F synthase (AKR1C3).

Prostaglandin H(2) (PGH(2)) formed from arachidonic acid is an unstable intermediate and is efficiently converted into more stable arachidonate metabolites (PGD(2), PGE(2), and PGF(2)) by the action of three groups of enzymes. Prostaglandin F synthase (PGFS) was first purified from bovine lung and catalyzes the formation of 9 alpha,11 beta-PGF(2) from PGD(2) and PGF(2)(alpha) from PGH(2) in the presence of NADPH. Human PGFS is 3 alpha-hydroxysteroid dehydrogenase (3 alpha-HSD) type II and has PGFS activity and 3 alpha-HSD activity. Human lung PGFS has been crystallized with the cofactor NADP(+) and the substrate PGD(2), and with the cofactor NADPH and the inhibitor rutin. These complex structures have been determined at 1.69 A resolution. PGFS has an (alpha/beta)(8) barrel structure. The cofactor and substrate or inhibitor bind in a cavity at the C-terminal end of the barrel. The cofactor binds deeply in the cavity and has extensive interactions with PGFS through hydrogen bonds, whereas the substrate (PGD(2)) is located above the bound cofactor and has little interaction with PGFS. Despite being largely structurally different from PGD(2), rutin is located at the same site of PGD(2), and its catechol and rhamnose moieties are involved in hydrogen bonds with PGFS. The catalytic site of PGFS contains the conserved Y55 and H117 residues. The carbonyl O(11) of PGD(2) and the hydroxyl O(13) of rutin are involved in hydrogen bonds with Y55 and H117. The cyclopentane ring of PGD(2) and the phenyl ring of rutin face the re-side of the nicotinamide ring of the cofactor. On the basis of the catalytic geometry, a direct hydride transfer from NADPH to PGD(2) would be a reasonable catalytic mechanism. The hydride transfer is facilitated by protonation of carbonyl O(11) of PGD(2) from either H117 (at low pH) or Y55 (at high pH). Since the substrate binding cavity of PGFS is relatively large in comparison with those of AKR1C1 and AKR1C2, PGFS (AKR1C3) could catalyze the reduction and/or oxidation reactions of various compounds over a relatively wide pH range.

20-Hydroxysteroid Dehydrogenases↗